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Vacation Rentals in Kailua, Oahu, Hawaii

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Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 89 Rentals in Kailua
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$330
Per Night
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1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details
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$145
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 3
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$146
Per Night
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Studio, 1 Bathroom, Sleeps 2
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Also consider
Kailua Beachfront - Spacious Family Home in Kailua's Best Location
5 Bedrooms, sleeps 14
$1,600 - $1,950 / night
Hawaii Kailua Beachside Luxury Home
7 Bedrooms, sleeps 14
$1,250 - $1,600 / night
Kakela Kai 4BR,Kailua Beachfront, A/C
4 Bedrooms, sleeps 8
$775 - $850 / night
Kailua Retreat
4 Bedrooms, sleeps 12
$399 / night
From
$800
Per Night
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8 Bedrooms, 4 Bathrooms, Sleeps 18
18 photos Details
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$126
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 2
16 photos Details
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$395
Per Night
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3 Bedrooms, 3 Bathrooms, Sleeps 7
16 photos Details
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$179
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 3
16 photos Details
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$265
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 4
13 photos Details
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From
$255
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 3
18 photos Details
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$95
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
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From
$95
Per Night
Response Rate: 100%
Studio, 1 Bathroom, Sleeps 2
10 photos Details
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From
$174
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 3
21 photos Details
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$165
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 2
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From
$120
Per Night
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Studio, 1 Bathroom, Sleeps 2
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$425
Per Night
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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$285
Per Night
Response Rate: 95%
7 Bedrooms, 5 Bathrooms, Sleeps 20
26 photos Details
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$399
Per Night
Response Rate: 95%
3 Bedrooms, 2 Bathrooms, Sleeps 10
16 photos Details
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$80
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
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$150
Per Night
Response Rate: 90%
1 Bedroom, 1 Bathroom, Sleeps 4
18 photos Details
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$79
Per Night
Response Rate: 90%
1 Bedroom, 1 Bathroom, Sleeps 3
25 photos Details
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$225
Per Night
Response Rate: 90%
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$139
Per Night
Response Rate: 88%
Studio, 1 Bathroom, Sleeps 3
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From
$165
Per Night
Response Rate: 86%
Studio, 1 Bathroom, Sleeps 2
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From
$175
Per Night
Response Rate: 86%
Studio, 1 Bathroom, Sleeps 4
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$200
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Studio, 1 Bathroom, Sleeps 3
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From
$250
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
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From
$150
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1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
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From
$200
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
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From
$147
Per Night
Response Rate: 100%
Studio, 1 Bathroom, Sleeps 3
17 photos Details
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From
$300
Per Night
Response Rate: 100%
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
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From
$1,250
Per Night
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4 Bedrooms, 4 Bathrooms, Sleeps 8
12 photos Details
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From
$550
Per Night
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3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
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From
$95
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
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From
$695
Per Night
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3 Bedrooms, 4 Bathrooms, Sleeps 8
26 photos Details
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$220
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 3
18 photos Details
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From
$900
Per Night
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5 Bedrooms, 4 Bathrooms, Sleeps 10
19 photos Details
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From
$125
Per Night
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5 Bedrooms, 5 Bathrooms, Sleeps 10
20 photos Details
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From
$100
Per Night
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3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
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From
$1,325
Per Night
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6 Bedrooms, 4 Bathrooms, Sleeps 14
29 photos Details
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From
$175
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
41 photos Details
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Suitability

  • Wheelchair access (8)
  • Elder access (29)
  • Suitable for children (35)
  • Pet friendly (2)
  • Smoking allowed (0)

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  • Internet (74)
  • Grill (67)
  • Other outdoor space (59)
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Book Online(41)

Suitability

  • Wheelchair access (8)
  • Elder access (29)
  • Suitable for children (35)
  • Pet friendly (2)
  • Smoking allowed (0)

Amenities

  • Internet (74)
  • Grill (67)
  • Other outdoor space (59)
  • Parking (51)
  • Washer/Dryer (51)
  • View all amenities
Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.